This invention relates to the production of bis-sulfonium salts of amino substituted bis(halomethyl) benzene compounds which are precursors for polymers with electrical and/or third order non-linear optical (NLO) properties, and is particularly concerned with the preparation of novel bis-sulfonium salts of amino substituted bis(halomethyl)benzene as precursors for conjugated amino substituted phenylene vinylene polymers having the above characteristics.
Polymers with electrical properties can be used for electromagnetic shielding, electronic counter measures, electrical device fabrication, and optical switching. Polymers with third order NLO properties can be used in smart skins, eye protection and optical switching.
The U.S. Pat. Nos. 4,599,193, 4,626,588 and 4,528,118 give some information on the synthesis of sulfonium salt precursors of poly(para-phenylene vinylene), (PPV), and the synthesis of sulfonium salt precursors of substituted PPV's. However, they do not teach the incorporation of amino substituents into the the sulfonium salt precursors, nor do they claim sulfonium salts of amino substituted bis(halomethyl) benzene as part of their invention.
In the article "Synthesis and Electrical Conductivity of AsF.sub.5 -Doped Poly(Arylene Vinylenes)" by S. Antoun, et al., Polymer Bulletin, 15,181-184 (1986), a series of polymers containing 2,5- disubstituted phenylene vinylene units, and the polymer containing 1,4-naphthalene vinylene units, were prepared by polymerization of their bis(sulfonium salts) through a base elimination reaction in solution. Films of these polymers were cast from aqueous solution and chemically treated (doped) with AsF.sub.5 vapor. The electrical conductivity of the doped films varied greatly with changes in polymer structure. The preparation of poly( 1,4-naphthalene-vinylene) is also disclosed in the article "Preparation and Electrical Conductivity of Poly(1,4 Naphthalene Vinylene)" by S. Antoun, et al., Journal of Polymer Science: Part C: Polymer Letters, Vol 24, 503-509, (1986). The preparation of dimethyl 2-(N,N-dimethylamino)terephthalate is described in H. Kauffmann, et al., Justus Liebig's Annalen der Chemie, 26, 393 ( 1912).
One object of the present invention is the provision of novel polymers having non-linear optical properties and/or electrical conductivity properties, and amino substituted bis(halomethyl)benzene precursors of such polymers.
Another object is to provide certain sulfonium salts of amino substituted bis(halomethyl)benzene compounds.